1 large fresh pineapple (about 3 pounds)
1 tablespoon canola oil
1 (7-ounce) can chipotles in adobo sauce, divided
2 tablespoons honey
4 (6 ounce) boneless, skinless chicken breasts
1 teaspoon salt, divided
2 medium ripe avocados, cut into wedges
Step 1: Cut Pineapple
Peel and core the pineapple. Cut the pineapple flesh into planks about 1 inch thick and 3 inches long to about 2 cups. Place the sliced pineapple, oil and 1 tablespoon adobo in a medium bowl; toss until combined.
Step 2: Chop Pineapple and add to bowl
Finely chop more pineapple to about 1/4 cup. Transfer the chopped pineapple to a large bowl along with any accumulated juices. (Reserve remaining pineapple for another use.)
Step 3: Marinade Chicken
Finely chop 2 to 3 chipotles to yield roughly 2 tablespoons; add to the large bowl with the chopped pineapple. Whisk in honey and 1/4 cup adobo. (Reserve remaining chipotles and adobo for another use.) Add chicken; toss to coat. Cover and let stand at room temperature for 15 minutes.
Step 4: Grill Pineapple Slices
Preheat grill to high (450°F to 500°F). Remove the pineapple planks from the marinade; place on oiled grates (reserve remaining marinade). Grill, uncovered, turning once, until charred and tender, 2 to 3 minutes per side. Transfer to a large platter.
Step 5: Grill Chicken
Remove the chicken from the marinade. Then sprinkle with 3/4 teaspoon salt (discard chicken marinade). Grill the chicken on oiled grates, uncovered and turning once, until the outside is caramelized, and an instant-read thermometer inserted into the thickest portion registers 165°F, 6 to 8 minutes per side. Brush the tops of the breasts with the reserved pineapple marinade; grill for 1 minute more. Transfer to the platter with the pineapple.
Step 6: Serve
Serve the chicken breasts whole or sliced with the grilled pineapple and fresh avocado. Season everything evenly with remaining 1/4 teaspoon salt before serving.